Influence of amide versus ester linkages on the properties of eight-armed PEG-PLA star block copolymer hydrogels

Biomacromolecules. 2010 Jan 11;11(1):224-32. doi: 10.1021/bm901080d.

Abstract

Water-soluble eight-armed poly(ethylene glycol)-poly(l-lactide) star block copolymers linked by an amide or ester group between the PEG core and the PLA blocks (PEG-(NHCO)-(PLA)(8) and PEG-(OCO)-(PLA)(8)) were synthesized by the stannous octoate catalyzed ring-opening polymerization of l-lactide using an amine- or hydroxyl-terminated eight-armed star PEG. At concentrations above the critical gel concentration, thermosensitive hydrogels were obtained, showing a reversible single gel-to-sol transition. At similar composition PEG-(NHCO)-(PLA)(8) hydrogels were formed at significantly lower polymer concentrations and had higher storage moduli. Whereas the hydrolytic degradation/dissolution of the PEG-(OCO)-(PLA)(8) takes place by preferential hydrolysis of the ester bond between the PEG and PLA block, the PEG-(NHCO)-(PLA)(8) hydrogels degrade through hydrolysis of ester bonds in the PLA main chain. Because of their relatively good mechanical properties and slow degradation in vitro, PEG-(NHCO)-(PLA)(8) hydrogels are interesting materials for biomedical applications such as controlled drug delivery systems and matrices for tissue engineering.

MeSH terms

  • Amides / chemistry*
  • Biocompatible Materials
  • Esters / chemistry*
  • Hydrogels / chemistry*
  • Magnetic Resonance Spectroscopy
  • Polyesters / chemistry*
  • Polyethylene Glycols / chemistry*
  • Polymers / chemistry*
  • Rheology

Substances

  • Amides
  • Biocompatible Materials
  • Esters
  • Hydrogels
  • Polyesters
  • Polymers
  • Polyethylene Glycols
  • poly(lactide)